Impact of molecular packing rearrangement on solid-state fluorescence: polyhalogenated N-hetarylamines vs. their co-crystals with 18-crown-6

CrystEngComm ◽  
2019 ◽  
Vol 21 (39) ◽  
pp. 5931-5946 ◽  
Author(s):  
Tamara A. Vaganova ◽  
Yurij V. Gatilov ◽  
Enrico Benassi ◽  
Igor P. Chuikov ◽  
Denis P. Pishchur ◽  
...  
Keyword(s):  
Solid State ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Molecular Packing ◽  
Solid State Fluorescence

Relationship between the hetarylamine chemical structure, crystal packing in homo- and co-crystals, and fluorescence effects (quenching, bathochromic and hypsochromic shifts).

The Influence of Nitrogen Position on Charge Carrier Mobility in Enantiopure Aza[6]helicene Crystals

2018 ◽  
Author(s):  
Francesco Salerno ◽  
Beth Rice ◽  
Julia Schmidt ◽  
Matthew J. Fuchter ◽  
Jenny Nelson ◽  
...  
Keyword(s):  
Solid State ◽  
Charge Carrier ◽  
Carrier Mobility ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Charge Carrier Mobility ◽  
Individual Factor ◽  
Charge Mobility ◽  
Order Of Magnitude ◽  
Small Change

<p>The properties of an organic semiconductor are dependent on both the chemical structure of the molecule involved, and how it is arranged in the solid-state. It is challenging to extract the influence of each individual factor, as small changes in the molecular structure often dramatically change the crystal packing and hence solid-state structure. Here, we use calculations to explore the influence of the nitrogen position on the charge mobility of a chiral organic molecule when the crystal packing is kept constant. The transfer integrals for a series of enantiopure aza[6]helicene crystals sharing the same packing were analysed in order to identify the best supramolecular motifs to promote charge carrier mobility. The regioisomers considered differ only in the positioning of the nitrogen atom in the aromatic scaffold. The simulations showed that even this small change in the chemical structure has a strong effect on the charge transport in the crystal, leading to differences in charge mobility of up to one order of magnitude. Some aza[6]helicene isomers that were packed interlocked with each other showed high HOMO-HOMO integrals (up to 70 meV), whilst molecules arranged with translational symmetry generally afforded the highest LUMO-LUMO integrals (40 - 70 meV). As many of the results are not intuitively obvious, a computational approach provides additional insight into the design of new semiconducting organic materials.</p>

Molecular Packing and Solid-State Fluorescence of Alkoxy-Cyano Substituted Diphenylbutadienes:  Structure of the Luminescent Aggregates

2008 ◽  
Vol 112 (6) ◽  
pp. 2137-2146 ◽  
Author(s):  
Riju Davis ◽  
N. S. Saleesh Kumar ◽  
Shibu Abraham ◽  
C. H. Suresh ◽  
Nigam P. Rath ◽  
...  
Keyword(s):  
Solid State ◽  
Molecular Packing ◽  
Solid State Fluorescence

Molecular Packing and Solid-state Fluorescence of Conjugated Compounds of Carbazole-acrylonitrile Derivatives

2014 ◽  
Vol 4 (1) ◽  
pp. 137-150 ◽  
Author(s):  
Maria Percino ◽  
Victor Chapela ◽  
Margarita Ceron ◽  
Guillermo Soriano-Moro ◽  
Maria Castro ◽  
...  
Keyword(s):  
Solid State ◽  
Molecular Packing ◽  
Solid State Fluorescence ◽  
Conjugated Compounds

Polyhalogenated aminobenzonitriles vs their co-crystals with 18-crown-6: amino group position as a tool to control crystal packing and solid-state fluorescence

CrystEngComm ◽  
2022 ◽  
Author(s):  
Tamara Vaganova ◽  
Enrico Benassi ◽  
Yuri V Gatilov ◽  
Igor P. Chuikov ◽  
Denis P Pishchur ◽  
...  
Keyword(s):  
Solid State ◽  
Supramolecular Structure ◽  
Crystal Packing ◽  
Amino Group ◽  
Group Position ◽  
Solid State Fluorescence

A series of para- and ortho-aminobenzonitriles differing in the nature and number of halogen substituents was used to synthesize 2:1 co-crystals with 18-crown-6 ether. Supramolecular structure of the obtained co-crystals...

The relationship between solid-state fluorescence intensity and molecular packing of coumarin dyes

2009 ◽  
Vol 82 (3) ◽  
pp. 258-267 ◽  
Author(s):  
So-Yeon Park ◽  
Masahiro Ebihara ◽  
Yasuhiro Kubota ◽  
Kazumasa Funabiki ◽  
Masaki Matsui
Keyword(s):  
Solid State ◽  
Fluorescence Intensity ◽  
Molecular Packing ◽  
Solid State Fluorescence ◽  
The Relationship ◽  
Coumarin Dyes

The Influence of Nitrogen Position on Charge Carrier Mobility in Enantiopure Aza[6]helicene Crystals

2018 ◽  
Author(s):  
Francesco Salerno ◽  
Beth Rice ◽  
Julia Schmidt ◽  
Matthew J. Fuchter ◽  
Jenny Nelson ◽  
...  
Keyword(s):  
Solid State ◽  
Charge Carrier ◽  
Carrier Mobility ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Charge Carrier Mobility ◽  
Individual Factor ◽  
Charge Mobility ◽  
Order Of Magnitude ◽  
Small Change

<p>The properties of an organic semiconductor are dependent on both the chemical structure of the molecule involved, and how it is arranged in the solid-state. It is challenging to extract the influence of each individual factor, as small changes in the molecular structure often dramatically change the crystal packing and hence solid-state structure. Here, we use calculations to explore the influence of the nitrogen position on the charge mobility of a chiral organic molecule when the crystal packing is kept constant. The transfer integrals for a series of enantiopure aza[6]helicene crystals sharing the same packing were analysed in order to identify the best supramolecular motifs to promote charge carrier mobility. The regioisomers considered differ only in the positioning of the nitrogen atom in the aromatic scaffold. The simulations showed that even this small change in the chemical structure has a strong effect on the charge transport in the crystal, leading to differences in charge mobility of up to one order of magnitude. Some aza[6]helicene isomers that were packed interlocked with each other showed high HOMO-HOMO integrals (up to 70 meV), whilst molecules arranged with translational symmetry generally afforded the highest LUMO-LUMO integrals (40 - 70 meV). As many of the results are not intuitively obvious, a computational approach provides additional insight into the design of new semiconducting organic materials.</p>

Unraveling the unusual effect of fluorination on crystal packing in an organic semiconductor

2020 ◽  
Vol 22 (3) ◽  
pp. 1665-1673 ◽  
Author(s):  
Ekaterina A. Komissarova ◽  
Dmitry I. Dominskiy ◽  
Vladimir E. Zhulanov ◽  
George G. Abashev ◽  
Afzal Siddiqui ◽  
...  
Keyword(s):  
Organic Semiconductor ◽  
Chemical Structure ◽  
Crystal Packing ◽  
Molecular Packing ◽  
Pi Stacking ◽  
Unusual Effect ◽  
Naphthalene Diimide

Two-atom variation in the chemical structure of a naphthalene diimide derivative induced an unexpected crossover from pi-stacking to herringbone molecular packing.

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